Meeting with an Ivy Exec Mentor? 7 Types of Questions to Get the Most Out of Your Session

No matter what stage you’re in professionally, you need a mentor. Even if you’ve made progress up the career ladder, a mentor can provide you valuable ideas about how to build your skills, reach goals, and make career decisions. 

Your mentor might be someone you meet at work, or in your professional network. If you haven’t found someone in your circles to serve as your mentor, however, you may decide to connect with someone who bills themselves specifically as a mentor. Here’s some advice about how to decide if you’re looking for a coach or a mentor. 

Whether you decide to connect with an Ivy Exec Mentor or find someone on your own, your objective is to make sure they offer you the most valuable advice possible. How do you do this? By asking key questions. 

What to Ask Your Mentor

Getting-to-know-you questions

Take the time to get to know who your Mentor is. For one, you want to make sure they have a professional background relevant to you. You also want to make sure you tell them about yourself and your goals to ensure you’re a strong match. 

• What were your goals in college? How have they stayed the same and different throughout your career? 
• What was the biggest risk you ever took? Did it pay off? 
• What skills have you found the most important in your career? How did you develop them? 

Establishing the mentorship relationship questions

Some of these questions will establish what your mentor has gleaned from their own mentorship relationships. This knowledge will help you understand what types of guidance they will likely offer you, as well. What’s more, you can ask questions about the boundaries of your professional relationship, including the frequency of your meetings and the topics of discussion. 

• Who has mentored you? 
• What have you learned from your mentors? 
• What do you think is the purpose of a mentorship? 
• How formal do you want this mentorship to be? 
• How often would you expect me to reach out?
• When do you think it’s best to connect with a mentor? 

Questions about your professional self

A mentorship is particularly valuable when your mentor can offer you valuable feedback about your strengths and weaknesses. For instance, you could show your mentor your job application materials, and they could let you know what to tweak to be more successful. 

• How does upper management view me? 
• What are three things that I do well? 
• What are three things I need to improve? 
• Is there something about me or my work history that may prevent me from advancing? 

Questions that help you build your skills

These questions should focus on your professional development both in your day-to-day professional life, as well as considering courses you may need to take or books you need to read to advance in your career. 

• What professional development have you done that was most useful to your career future? 
• What courses have you taken that have been most useful to you? 
• Are there skills that you think I should develop for my career future? 
• Are there any “secret” qualifications in our field that you think I lack or are underdeveloped? 

Questions about your current work situation

When it comes to what to ask a mentor, questions like these top the list. You may also want to turn to your mentor to ask questions about tricky situations in your current role.

• I don’t feel confident leading my team. What should I do? 
• I want to build my management capacity, but I don’t supervise anyone. What steps can I take? 
• My boss told me I should develop my ____ skill. How would you go about this? 
• My boss is micromanaging me. How can I ask them to stop? 
• I need to get buy-in from my team about a new initiative. How can I get it? 
• I want to ask for a raise. Can we practice that scenario? 

Questions about your immediate next steps

The ideal mentor will be someone who can coach you through career advancements both short- and long-term. These questions should focus on jobs you may want to apply for right away or as your career next step. 

• There are two roles open that would lead me down different career paths. Which one do you think I should choose for my long-term future? 
• I want to transition to the next step in my career. Do you have any suggestions for roles that would fit me well? 

Questions about your professional future

Your mentor can also help you plan your extended career future. This means they can provide advice about how to get from where you’re at to the position you’re hoping for in the longer-term future. 

• I want a career like yours. What should I do to make that happen? 
• I’m not sure where I want to be in five or 10 years. Can we discuss it? 
• What does the career trajectory for someone in my field look like? Is it a straight path or are there multiple options? 

Finding a Professional Mentor

If you don’t have a professional mentor, or want to change mentors, consider connecting with one of Ivy Exec’s Mentors. Our Mentors are all senior-level executives excited about answering questions and shaping your professional future. They can also guide you on your path to knowing what to ask a mentor. 

Speaking about her mentorship, Rona said, “Mentoring was the most important step I’ve taken. It’s definitely accelerated my career plans, and I’m moving forward confidently with new approaches I think will yield positive results.”